Winchester Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Winchester

Property grounds
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
Dreamtime - Modern A-frame Cabin w/ Hot tub
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
10.0 out of 10, Exceptional, (28)
"Very nice clean cabin in a very quiet location. enjoyed our stay watching the deer come by everyday and other wildlife."
The price is $145
$330 total
includes taxes & fees
May 22 - May 23
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
Interior
Escape to Shenandoah River, Hot Tub after a Hike!
10.0 out of 10, Exceptional, (38)
"Super clean. Super easy check in & check out. Quiet and beautiful setting. The windows bring the outdoors in. Fabulous to watch the electric storm through those big beautiful windows from the comfort of the couch."
The price is $147
$373 total
includes taxes & fees
Jun 5 - Jun 6
Escape to Shenandoah River, Hot Tub after a Hike!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Interior
Lake House w/ Pool and King Bed, Fishing - Dogs OK
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay, really nice place we enjoyed seeing the water"
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Pool
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, (273)
"Our stay was very relaxed, the property is in a nice location, nestled in the woods, with a nice amount of lawn in the front. We enjoyed the wildlife, and explored Luray caverns and some of the Shenandoah mountains. The cabin is very simple, but sufficient, and has essentials, although a cabinet somewhere would have been convenient. Thank you for making our great week possible, it was a blessing!"
The price is $215
$333 total
includes taxes & fees
May 27 - May 28
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Exterior
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (16)
"We had a nice stay in a lovely rural location with nice outdoor terrace and quiet street for a long walk. Communication with the host was simple and straight forward."
The price is $270
$391 total
includes taxes & fees
Jun 9 - Jun 10
18th Century Stone Cottage minutes from historic Middleburg
Property grounds
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
10.0 out of 10, Exceptional, (25)
"The pictures and description are 100% accurate, but being there in person to take in the peaceful surroundings and views of nature with the family was a great experience. The hostess was responsive from the moment we booked and provided all the info we needed to make it to this mountain top cabin on the VA/WV border. We drove up on a Friday and after getting out of DC traffic we were on our way to Almost Heaven cabin. When we’re about a mile or so from the cabin we saw a black bear crossing...
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
Property grounds
Pine Cone Cabin at Fort Valley
10.0 out of 10, Exceptional, (171)
"/0"
Pine Cone Cabin at Fort Valley
Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (144)
"Stayed here for a weekend for a mini honeymoon/wife’s birthday. The cabin had everything we needed and more. We stay at a lot of cabins around shenendoah valley and this one was definitely high on the list of quality. Very clean and cozy. We took a hike, enjoyed the fire pit and hot tub, grilled, and relaxed on the upper deck. All the appliances worked and shower was great. Our only issue was the bed was very noisy and sounded like it could use some attention or an upgrade, there was a good...
Secluded, Cozy Cottage in the Shenandoah Valley
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is $75
$144 total
includes taxes & fees
Jun 2 - Jun 3
❤️ Secluded 1940s Romantic Tiny House on the River
TV
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
10.0 out of 10, Exceptional, (11)
"This house is a dream!!! Loved everything about it and Ronnie was so accommodating, loved every moment of it"
The price is $500
$902 total
includes taxes & fees
May 23 - May 24
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
Property grounds
Beautiful 360 views!
10.0 out of 10, Exceptional, (155)
"Super quaint little cottage, exactly what we needed. The hosts are incredibly sweet and accommodating. The view is of open farmland with mountians in the distance. The sun sets off the back of the cottage and theres a wonderful view. Really wonderful spot!"
Beautiful 360 views!
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (142)
"The property was exactly as described. The house was lovely and well appointed. our friends and I had a wonderful time."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
2 bedrooms, WiFi, bed sheets
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, (265)
"The place is amazing, great view to the river, night view is gorgeous, my kids had a lot of fun here, we will come back"
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Exterior
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (244)
"We really enjoyed the property. It was clean. Internet worked well. Washer and dryer was nice. Too cold to enjoy the hot tub for me. My suggestions are a new shower head, thank goodness I didn’t have to wash my hair. The flow is too spread out and not enough to efficiently rinse as you shower. Second is a cheaper Kcup machine would be nice. Traveling with ground coffee is not really ideal for a quick trip away. Third thing I suggest is two beach towels (minimum) for the use of the hot tub. We...
The price is $100
$313 total
includes taxes & fees
May 27 - May 28
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Fridge, microwave, oven, stovetop
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (227)
"Fantastic spot to spend a few days. Incredible house, fantastic amenities, and a beautiful location."
Breathtaking views with an indoor private pool, come escape with us
Property grounds
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (188)
"Beautiful quiet location. Very close to the forest, but unfortunately there is a large stream that runs across the trail that leads to GWNF. Otherwise, a nearly perfect place! The host's communication was great as well. We enjoyed the pool table (can be table tennis as well), and the variety of hikes a short drive away. Some of the furniture had animal hair on it from a previous guest. A deeper clean would have been appreciated, but it wasn't a major concern. We will consider visiting again in...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Property grounds
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (276)
"This cabin was very comfortable and clean! The kitchen was well equipped for all our needs. The views from the inside are just as spectacular on the outside. While the house is not directly on the reiver that was okay. We figured it would be hard to find a house right on the river with amazing views of the mountains off in the distance. The walk down to the river is not bad. It takes about 7 or so minutes. I highly recommend boots or something other than standard shoes if you go before the dew...
Star view cabin-Riverfront
Lake
Above The Rivers Edge Cabin #1
9.8 out of 10, Exceptional, (152)
"Had a fantabulos time! The cabin had everything we needed."
Above The Rivers Edge Cabin #1
Property grounds
Lost River Luxury Cabin in Wild Wonderful West Virginia-2 hour drive fr DC!
9.8 out of 10, Exceptional, (56)
"My friends and I were planning a getaway to reconnect and heal together. We have been friends for 30 years and had each suffered our own personal nightmares recently. It was going to be the first time we would all be in the same room in 8 years. We stumbled upon this beautiful house on VRBO and decided to go for it. Stacey responded promptly to our request to stay as well as to every question. The house was clean, comfortable and elegant. There was very little that we needed to leave the house...
Lost River Luxury Cabin in Wild Wonderful West Virginia-2 hour drive fr DC!
Don't see what you're looking for?
See all available properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Winchester you may be interested in

Exterior
Comfort Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (929)
"Nice place nice folks good breakfast clean rooms close to the interstate "
The price is $98
$107 total
includes taxes & fees
May 26 - May 27
Comfort Inn & Suites
Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1337)
"Beautiful !!! Way exceeded expectations ! Great price and gorgeous and clean rooms very modern layout ! Beautiful breakfast and pleasant staff. What a pleasure !!! "
The price is $115
$125 total
includes taxes & fees
May 26 - May 27
La Quinta Inn & Suites by Wyndham Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (769)
"Pool is cold, staff is super nice. Place is clean and very nice lots near it for food mall is only 8 min away. Breakfast was ok. Have stayed here several times and will continue to stay here as needed."
The price is $84
$92 total
includes taxes & fees
Jun 2 - Jun 3
Microtel Inn & Suites by Wyndham Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home rental near Winchester is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Winchester?

Choose from 13 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of family-friendly sights, whereas cultural attractions include Museum of the Shenandoah Valley and Bright Box Theater. Other places in town to visit include Jim Barnett Park and Apple Blossom Mall.

What’s a vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.

Recent reviews of Winchester properties
Expedia verified reviews

Lansdowne Resort and Spa

Lansdowne Resort and Spa

5/5 Excellent
Experience the country vibe
"Great space, excellent attention, gerogous location and ambiance"
A verified traveler stayed at Lansdowne Resort and Spa
Posted 15 hours ago
Lansdowne Resort and Spa